Bridged tetrahydroisoquinolines as selective NADPH oxidase 2 (Nox 2) inhibitors

Eugenia Cifuentes-Pagano; Jaideep Saha; Gábor Csányi; Imad Al Ghouleh; Sanghamitra Sahoo; Andrés Rodríguez; Peter Wipf; Patrick J. Pagano; Erin M. Skoda

doi:10.1039/c3md00061c

Bridged tetrahydroisoquinolines as selective NADPH oxidase 2 (Nox ₂) inhibitors

Eugenia Cifuentes-Pagano, Jaideep Saha, Gábor Csányi, Imad Al Ghouleh, Sanghamitra Sahoo, Andrés Rodríguez, Peter Wipf, Patrick J. Pagano, Erin M. Skoda

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

(1SR,4RS)-3,3-Dimethyl-1,2,3,4-tetrahydro-1,4-(epiminomethano)naphthalenes were synthesized in 2-3 steps from commercially available materials and assessed for specificity and effectiveness across a range of Nox isoforms. The N-pentyl and N-methylenethiophene substituted analogs 11g and 11h emerged as selective Nox₂ inhibitors with cellular IC₅₀ values of 20 and 32 μM, respectively.

Original language	English (US)
Pages (from-to)	1085-1092
Number of pages	8
Journal	MedChemComm
Volume	4
Issue number	7
DOIs	https://doi.org/10.1039/c3md00061c
State	Published - Jul 2013
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Organic Chemistry

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title = "Bridged tetrahydroisoquinolines as selective NADPH oxidase 2 (Nox 2) inhibitors",

abstract = "(1SR,4RS)-3,3-Dimethyl-1,2,3,4-tetrahydro-1,4-(epiminomethano)naphthalenes were synthesized in 2-3 steps from commercially available materials and assessed for specificity and effectiveness across a range of Nox isoforms. The N-pentyl and N-methylenethiophene substituted analogs 11g and 11h emerged as selective Nox2 inhibitors with cellular IC50 values of 20 and 32 μM, respectively.",

author = "Eugenia Cifuentes-Pagano and Jaideep Saha and G{\'a}bor Cs{\'a}nyi and {Al Ghouleh}, Imad and Sanghamitra Sahoo and Andr{\'e}s Rodr{\'i}guez and Peter Wipf and Pagano, {Patrick J.} and Skoda, {Erin M.}",

year = "2013",

month = jul,

doi = "10.1039/c3md00061c",

language = "English (US)",

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journal = "MedChemComm",

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T1 - Bridged tetrahydroisoquinolines as selective NADPH oxidase 2 (Nox 2) inhibitors

AU - Cifuentes-Pagano, Eugenia

AU - Saha, Jaideep

AU - Csányi, Gábor

AU - Al Ghouleh, Imad

AU - Sahoo, Sanghamitra

AU - Rodríguez, Andrés

AU - Wipf, Peter

AU - Pagano, Patrick J.

AU - Skoda, Erin M.

PY - 2013/7

Y1 - 2013/7

N2 - (1SR,4RS)-3,3-Dimethyl-1,2,3,4-tetrahydro-1,4-(epiminomethano)naphthalenes were synthesized in 2-3 steps from commercially available materials and assessed for specificity and effectiveness across a range of Nox isoforms. The N-pentyl and N-methylenethiophene substituted analogs 11g and 11h emerged as selective Nox2 inhibitors with cellular IC50 values of 20 and 32 μM, respectively.

AB - (1SR,4RS)-3,3-Dimethyl-1,2,3,4-tetrahydro-1,4-(epiminomethano)naphthalenes were synthesized in 2-3 steps from commercially available materials and assessed for specificity and effectiveness across a range of Nox isoforms. The N-pentyl and N-methylenethiophene substituted analogs 11g and 11h emerged as selective Nox2 inhibitors with cellular IC50 values of 20 and 32 μM, respectively.

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DO - 10.1039/c3md00061c

M3 - Article

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SN - 2040-2503

VL - 4

SP - 1085

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JO - MedChemComm

JF - MedChemComm

IS - 7

ER -

Bridged tetrahydroisoquinolines as selective NADPH oxidase 2 (Nox ₂) inhibitors

Abstract

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